Sodium Azide → tert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamate

HRID 1244726Notes

Reaction equation

HRID 1244726 reaction equation
[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][C@@H:9]1OS(C)(=O)=O)=[O:6])[CH3:3].[N-:23]=[N+]=[N-].[Na+]>CC(N(C)C)=O.C(OCC)(=O)C>[NH2:23][C@@H:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:8]1[NH:7][C:5]([O:4][C:2]([CH3:22])([CH3:3])[CH3:1])=[O:6]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86338034(1R,2s)-1-(tert-butoxycarbonylamino)-2,3-dihydro-1H-inden-2-yl methanesulfonate

Product 1

HCID 11299644tert-butyl ((1R,2R)-2-amino-2,3-dihydro-1H-inden-1-yl)carbamateYield 98%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

Cis-1-[(1,1-dimethylethoxy)carbonylamino]-2-methanesulphonyloxyindan (18.1 g, 55.3 mmol) was dissolved in dry dimethyl acetamide (100 ml). Sodium azide (5.4 g, 83.0 mmol) was added and the mixture heated to 90° C. for 6 hours. The reaction was cooled, diluted with ethyl acetate (150 ml), washed with water (6×200 ml) and dried over magnesium sulphate. 10% Palladium on activated carbon was added and the mixture stirred under a hydrogen atmosphere for 24 hours. Filtration through celite followed by evaporation gave the title compound (2.6 g, 98%) as a white solid.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with water (6×200 ml)
  3. dry with materialdried over magnesium sulphate
  4. addition10% Palladium on activated carbon was added
  5. filtrationFiltration through celite
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-1659daa6b81c42609b6bac6e9f1847fb
Source dataset
uspto-grants-2006_10
Patent number
US07122567B2

Reaction notes

Loading…